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Gas chromatography mass spectrometry of some thermally labile urea pesticides.

The application of gas chromatography/mass spectrometry to three thermally labile phenylurea pesticides is reported. Using alcohols as solvents the decomposition of the pesticides is followed by a reaction in which esters of N-(3,4-dichlorophenyl)carbamic acid are formed. As these reactions occur during the gas chromatographic analysis, it is the esters which are identified in the mass spectrometer. The methyl ester is itself a pesticide so an erroneous conclusion about the original pesticide could be reached when methanol is the solvent.

Diuron

[Studies on the embryotoxicity of monolinuron and buturon in NMRI-mice (author's transl)].

The acute LD50 in virginal NMRI-Mice was found to be 2528 mg/kg for monolinuron and 1791 mg/kg for buturon. Pregnant female mice of the NMRI strain were administered orally 25--1000 mg monolinuron/kg (I) and 100-400 mg buturon/kg (II) on days 6--15 of gestation and, during defined phases of fetal development (days 10--13 after conception), 500 mg I/kg and 350 mg II/kg. Following administration of 10 doses, an increase of postimplantative losses and clear retardation of development in the upper dose range from 100 mg I/kg and 300 mg II/kg as well as a dose-dependent increase of the rate of cleft palates could be observed. High doses of both substances given from day 6--15 of pregnancy produced minor numbers of wavy and fused ribs as well as hypoplasia of the upper jaw after application of monolinuron and exenteria and exencephaly after buturon. Administration of monolinuron between days 10 and 13 of gestation resulted a minor and that of buturon a clear increase of the number of cleft palates. To evaluate postnatal development 200 and 500 mg I/kg, and 200 and 300 mg II/kg were administered orally on days 6--15 of gestation. In the higher doses, both substances produced an increased mortality among the offspring up to 3 weeks after birth, and a clear increase of the rate of cleft palates.

Abnormalities, Drug-Induced

A comparative study on pesticide formulations for application in running waters.

Release rates into water of monolinuron, desmetryne, and carbofuran from three different types of formulations have been studied to control aquatic weeds in running waters. The migration of active ingredients (AI) from conventional wettable powder formulations was complete within 1 day, while the migration from ethylene-vinyl acetate copolymeric matrix (EVA) lasted significantly longer due to low diffusion coefficients of monomeric pesticides in polymeric matrices Do = 10(-8)-10(-12) (cm2 X sec-1). The herbicidal action could be extrapolated up to several years. Release duration of AI from calcium alginate beads lasted 2 weeks. Herbicidal effectiveness of terbutryne-EVA formulation has been investigated in a laboratory-scale simulated flow system device with duckweed plants (Lemna minor) as test organism. Growth inhibition of duckweed could be achieved at approx 20 ppb terbutryne in steady state.

Absorption

Fate of [14C]monolinuron in potatoes and soil under outdoor conditions.

[phenyl-14C]Monolinuron was applied (2.5 and 1.9 kg/ha) to the soil surface of an outdoor lysimeter in two successive years: then, potatoes were grown. Total recovery of 14C in soil, plants, and leached water was about 55% (of 14C applied) after the first growing period and about 43% after the second growing period. Radioactivity in soil contained 77.1% (based on total 14C recovered in soil) bound residues, 15% monolinuron, and the following conversion products: N-(4-hydroxyphenyl)-N'-methoxy-N'-methylurea, N-(4-chlorophenyl)-N'-methylurea. N-(4-chlorophenyl)methylcarbamate, N-(4-chlorophenyl)-N-methyl-methylcarbamate, and 4-chloroformanilide. The leachate contained 0.8% (based on total 14C recovered in leachate) N-(4-hydroxyphenyl)-N'-methoxy-N'-methylurea. Potato plants contained 0.106 mg/kg radioactive residues in peeled tubers after one growing period and 15.94 mg/kg in the tops; after two growing periods, peeled tubers contained 0.091 mg/kg and tops contained 18.87 mg/kg radioactive residues. These residues consisted of bound 14C (57.9% of total 14C recovered in plants), N-(4-hydroxyphenyl)-N'-methoxy-N'-methylurea, N-(4-chlorophenyl)-N'-methylurea, N-(4-chlorophenyl)methylcarbamate, N-(4-chlorophenyl)-N-methyl-methylcarbamate, and 4,4'-dichlorozobenzene.

Biodegradation, Environmental

[Biotransformation of monolinuron (N-(4-chlorophenyl)-N'-methyl-N'methoxyurea) in isolated perfused chicken liver].

The biotransformation of radioactively labelled monolinuron (N-(4-chloro[U-14C]phenyl)-N'-methyl-N'-methoxyurea) was studied in the isolated perfused liver of the chicken. After a 4-hr perfusion, 83.1% of the added radioactivity was recovered, 56.6% in the perfusion medium and 26.5% in the liver and bile. The fraction of radioactivity extractable from the perfusion medium into ethyl acetate amounted to 47.8% of the added dose. In addition to monolinuron, five breakdown products were identified in this extract, namely N-(4-chlorophenyl)-N'-hydroxymethyl-N'-methoxyurea, N-(4-chlorophenyl)-N'-methoxyurea, N-(4-chlorophenyl)-N'-methylurea, 4-chlorophenylurea and 4-chloroacetanilide. Of particular interest was the absence of arylhydroxylated monolinuron derivatives, since in monolinuron-metabolism studies in the laying hen 2-hydroxy-4-chlorophenylurea and 3-hydroxy-4-chlorophenylurea were both detected. This differing metabolism corresponds to earlier findings in the rat, in which arylhydroxylated breakdown products were detected only in in vivo studies and not in rat-liver perfusion. Possible reasons for the differing metabolism of monolinuron in vivo and in vitro are discussed.

Animals